SYNTHESIS OF NEW SPIROOXINDOLOPYRROLIDINES VIA THREE-COMPONENT REACTION OF ISATINS, α-AMINO ACIDS, AND (<i>E</i>)-3-ARYL-2-CYANOACRYLAMIDES OR (<i>E</i>)-3-ARYL-2-(4-ARYLTHIAZOL-2-YL)ACRYLONITRILES

Authors

  • Tetyana L. Pavlovska State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61002
  • Victoria V. Lipson V. Ya. Danilevsky Institute of Endocrine Pathology Problems, Academy of Medical Sciences of Ukraine, 10 Alchevskih St., Kharkiv 61002
  • Svetlana V. Shishkina State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61002
  • Vladimir I. Musatov State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61002
  • Julia A. Nichaenko V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61077
  • Victor V. Dotsenko Kuban State University, 149 Stavropolskaya St., Krasnodar 350040

DOI:

https://doi.org/10.1007/3602

Keywords:

azomethine ylide, cyanoacrylamide, sarcosine, spiro[indoline-3, 2'-pyrrolidin]-2-one, thiazoleacrylonitrile

Abstract

A series of novel spirooxindolopyrrolidine derivatives has been prepared via a three-component 1,3-dipolar cycloaddition reaction of 2-oxindoleazomethine ylides generated in situ from isatin and sarcosine or valine with (E)-3-aryl-2-cyanoacrylamides or (E)-3-aryl-2-(4-arylthiazol-2-yl)acrylonitriles as dipolarophiles. To rationalize the observed regio- and stereoselectivity, calculations of the geometrical structures of all possible conformers and charge distribution in the reacting systems were performed.

Author Biography

Tetyana L. Pavlovska, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61002

аспирант

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Published

2017-05-02

Issue

Vol. 53 No. 4 (2017): Multicomponent reactions in the synthesis of heterocycles

Section

Original Papers